Hydroquinone → N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamide

HRID 1018900노트

반응식

HRID 1018900 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10](Br)[CH3:11].[C:15]1([CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[OH:16].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10]([O:16][C:15]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[CH3:11]

참가 물질

6

반응물 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 18183268HCID 18183268, 화합물

생성물 1

HCID 18183267N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamide수율 86.4%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6342Acetonitrile용매

실험 절차

N-(2-fluorophenyl)-N-methyl-2-bromopropionamide(18.2 g, 0.07 mol), hydroquinone(7 g, 0.064 mol), potassium carbonate(10.54 g, 0.076 mol) and tetra-n-butylammonium bromide(1 g) were dissolved in 350 ml of acetonitrile and heated at reflux for 6 hours. The reaction mixture was cooled to room temperature and solid remained during the reaction was filtered out. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography(eluent: ethyl acetate/n-hexane=1/2) to afford 16 g of the target product.

후처리

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. filtrationwas filtered out
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude product was purified by column chromatography(eluent

출처 및 근거

ORD 기록
ord-027d44da8d9f412483f59f282b3e1529
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486098B1

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